Here’s an article on condotels, where you can own a vacation property and potentially break even on cash flow:

“If you buy a unit and expect it to pay for itself, it won’t. We see these properties producing money to offset expenses like management and homeowner association fees, property taxes and liability coverage.”

The article mentions some good areas for Condotels: “Las Vegas, New York, Chicago and San Diego, and emerging markets in cities like Boston and Washington, D.C., and ‘2Â½-hour, drive-to locations’ such as the Napa Valley, Mexico and sites between N.J. and Maine.”